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Vacation Rentals in Kailua, HI

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All 107 Rentals in Kailua
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From
$139
Per Night
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1 / 7
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Studio, 1 Bathroom, Sleeps 2
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$199
Per Night
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 3
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$185
Per Night
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1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 2
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From
$126
Per Night
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1 / 16
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1 Bedroom, 1 Bathroom, Sleeps 2
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Details Reviews (5) Make Inquiry
Amenities & Details
  • Porch
  • Washer
  • Stove
  • Grill
  • Dryer
  • Refrigerator
  • Ceiling Fans
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Come and play at the Beach We are located in a prime residential neighborhood 2 blocks from Kailua Beach Park Entrance as well as downtown. And for those of you traveling without a car, a major bus line is just around the corner. Here you will be surrounded by lush landscaping and find comfort... View all property information
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5 of 5 stars Reviewed July 7, 2014
We enjoyed staying in this neat and clean studio apartment. Sabine and Ray were welcoming and have put a lot of thought into providing everything for guests' comfort. We loved...
4 of 5 stars Reviewed June 28, 2014
We spent 6 nights at Suite Aloha at the end of April. The studio apartment was very clean, nicely furnished and decorated in Hawaiian style. We made use of the large gas barbecue...
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From
$95
Per Night
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1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
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Details Reviews (3) Make Inquiry
Amenities & Details
  • Microwave
  • Washer
  • Pool
  • Internet Access
  • Satellite TV
  • Dryer
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This is a great 300 sq ft studio only 3 min drive to world famous kailua beach This studio has a cal king bed and a futon that can sleep 4 people 55 in flat screen TV free wi-fi kitchen with everything you need to cook all your meals natural stone shower that is very roomy and a tiled swimming... View all property information
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5 of 5 stars Reviewed September 28, 2014
John was an incredible host very resourceful and kind always there whenever my wife or I had a question told us all the good restaurants. Very happy great value, clean, bikes...
3 of 5 stars Reviewed July 6, 2014
Looking for a deal on our Hawaiian getaway, I booked this place after another fell through. I was trying to be thrifty and this looked like it fit our needs. The place is...
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From
$900
Per Night
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1 / 1
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5 Bedrooms, 3 Bathrooms, Sleeps 10
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Breath-taking views . . . luxurious details . . . This is Shangri-La by the Sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Rejuvenate your mind, and cherish friends and family as you settle into this luxurious,... View all property information
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From
$425
Per Night
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1 / 16
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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Details Reviews (2) Make Inquiry
Amenities & Details
  • Dryer
  • Microwave
  • Patio
  • Parking
  • Ceiling Fans
  • Satellite TV
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Experience Hawaii at it's fullest by staying at this amazing 1926 bungalow located between two of the most beautiful beaches in the world. Lanikai and Kailua beaches are just 200 yards away. Kayak, Bicycle, Surfboard, Paddle board and Snorkel Rentals are 200 yards away at Kailua Beach Park. A... View all property information
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5 of 5 stars Reviewed July 18, 2014
We had two families totaling 4 adults and 5 kids stay at this house, and had a fabulous time! The house is beautiful, and set right between two lovely beaches. The house is not...
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From
$225
Per Night
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1 / 22
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1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Pool
  • Dishwasher
  • Patio
  • Grill
  • Safe
  • Stove
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
LOCATION, LUXURY, PRIVACY, & SECURITY. KAILUA DREAMS-MAKAI is the PERFECT Vacation Rental for the discerning and well travelled guests. Guests will appreciate the location, luxury, privacy, and security our unit offers. We are conveniently located in a quiet neighborhood halfway between the... View all property information
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5 of 5 stars Reviewed September 21, 2014
We were a bit apprehensive about being the first renters of this new rental, but took a chance since the location and space seemed ideal. We had a wonderful week staying here...
5 of 5 stars Reviewed November 3, 2014
Apparetement avec piscine très propre et spacieux, accueil sympathique. Je n'hésiterai pas à y retourner.
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From
$1,250
Per Night
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1 / 24
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Wi-Fi
  • Parking
  • Boat Available
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Description Our BEACHFRONT home is designed to provide you with a perfect vacation retreat. The house is as close to the beach as you legally can build. The beach of Kailua is renown for its fine white sand, blue green waters and safety. This is not a crowded beach, but has a pleasant neighborhood... View all property information
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From
$145
Per Night
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1 / 32
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Reviews (13) Make Inquiry
Amenities & Details
  • Satellite TV
  • Refrigerator
  • Microwave
  • Washer
  • DVD Player
  • Parking
  • Dryer
  • Hairdryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Kailua Cove is a spacious, bright and cheery studio that sleeps 3 and offers: • Private entrance • 1 queen and 1 twin bed • Well-equipped kitchenette, including sink and full-size refrigerator/freezer • Private, indoor washer & dryer • Large walk-in, tile shower • 400+ square feet • Plenty of... View all property information
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5 of 5 stars Reviewed November 11, 2014
I used to live in Kailua, so I feel like I'm a good judge of where you should stay. If you plan on spending a good amount of your time on Kailua or Lanikai Beaches, this is a...
5 of 5 stars Reviewed October 31, 2014
The accommodations were large enough for myself, my husband, and my 20 something daughter. We were staying in Kailua to visit my son/daughter in law. It was clean, comfortable...
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From
$150
Per Night
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1 / 18
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (9) Make Inquiry
Amenities & Details
  • Grill
  • Patio
  • Internet Access
  • VCR
  • Refrigerator
  • Microwave
  • Satellite TV
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
A private 400 sq foot studio w/fenced courtyard/lanai, in quiet Kaimalino. Relax outdoors or indoors w/full kitchen, bath, cable and internet connections. A short walk will take you to a turtle nesting grounds, the open ocean facing Maui and Lanai islands, sandy Kailua Beach, and Aikahi Shopping... View all property information
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4 of 5 stars Reviewed August 13, 2014
This studio was exactly as advertised and more. It was an easy walk to a beautiful sunrise, supermarkets and restaurants but out of the way enough to avoid the traffic and noise...
5 of 5 stars Reviewed January 8, 2014
This proved a really great choice , the condo is lovely and in a really quiet and peaceful area. Plenty of space and a nice garden with plenty of seating . The owner lives next...
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From
$150
Per Night
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1 / 15
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1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
If you're looking for a perfect spot to call home during your stay in Kailua, you'll love this one bedroom/one bath apartment in walking distance of world-famous Kailua and Lanikai Beaches. This unit, which has just been made available as a monthly vacation rental, is tucked away in a quiet,... View all property information
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From
$174
Per Night
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1 / 12
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Make Inquiry
Amenities & Details
  • Pool
  • Grill
  • Air Conditioning
  • Ceiling Fans
  • Hairdryer
  • Parking
  • Outdoor Dining Area
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaii Sheffield House is located only 10 houses to Kailua Beach. Sheffield House provides a home away from home for your Kailua Hawaii vacation. The Garden Suite has free off street parking, free wifi, cable TV, boogie boards and a first morning complementary continental breakfast. The... View all property information
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From
$155
Per Night
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1 / 21
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1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Dryer
  • Grill
  • Stove
  • Ceiling Fans
  • Refrigerator
  • Hot Tub
  • Patio
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning one-bedroom. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$1,450
Per Night
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1 / 22
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Ceiling Fans
  • Air Conditioning
  • TV
  • Parking
  • Pool
  • Hot Tub
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This getaway’s name, Maluhia, translates into “Peace” in Hawaiian, and it’s not hard to see why—nestled in the region of Kailua, known for its turquoise waters, and white sandy beaches, you’ll feel relaxed in this tranquil space, it’s one of our top Oahu vacation rentals. The low-key area of Kailua... View all property information
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From
$149
Per Night
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1 / 12
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Studio, 1 Bathroom, Sleeps 5
Bookings
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Amenities & Details
  • Grill
  • Stereo System
  • Canoe
  • Pool
  • Ceiling Fans
  • Safe
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Spacious Studio with Private Entrance & Bathroom This beautiful studio is located in a quiet neighborhood close to world famous Kailua Beach. Property is on the water with a large swimming pool. The area is surrounded by lush tropical Gardens that offer many private seating areas for morning... View all property information
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From
$165
Per Night
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1 / 11
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Studio, 1 Bathroom, Sleeps 3
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our newly renovated studio is the perfect get-away located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or a couple, just minutes away from the beach by foot or bike. Kailua Seahorse Studio is PERFECT. It's even more beautiful in person than in the pictures.... View all property information
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From
$130
Per Night
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1 / 18
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry
Amenities & Details
  • Patio
  • Microwave
  • Stove
  • Dryer
  • Air Conditioning
  • Ceiling Fans
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Stroll along the white sandy beaches of Lanikai Beach, named one of the top 10 beaches in the world by 2014 Travelers Choice on Trip Advisor! Only a 5 minute drive from our stunning studio. We are situated on a picturesque, family-friendly road with little road noise and traffic. Breathtaking... View all property information
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From
$425
Per Night
View Details
1 / 18
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Make Inquiry
Amenities & Details
  • Microwave
  • Grill
  • Dishwasher
  • Patio
  • Parking
  • Safe
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • Smoking allowed
  • Elder access
  • x
About this property
This three bedroom Lanikai home, plus attached, but private entrance to a completely self contained studio with kitchenette and fully enclose courtyard, is just one short block to Lanikai Beach. Bring the family, and let the grandparents, friends be with you but also have the privacy they need! We... View all property information
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From
$225
Per Night
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1 / 12
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful Single Family Home is sought after neighborhood in Kailua. 15 minutes walk to the beach, Fully furnished with dishes, linens, kitchenware - everything you need. Accommodates 4-6 Some standout features are -- -- 2270 sq feet of house plus a yard that is about 1800 sq feet. -- beautiful... View all property information
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From
$800
Per Night
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1 / 18
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8 Bedrooms, 4 Bathrooms, Sleeps 18
Details Reviews (3) Make Inquiry
Amenities & Details
  • Patio
  • Microwave
  • Dryer
  • Hot Tub
  • Safe
  • Refrigerator
  • Grill
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The property is located approx. 10 miles from the city of Honolulu . 15 minutes walk to the nearest beach access. East of the island of Oahu . Surrounded by lush green mountains . The house has tranquil and peaceful atmosphere . This house is fully furnished in an authentic island style. The... View all property information
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4 of 5 stars Reviewed February 19, 2014
On our arrival we were met by Sonya (owner) with cup cakes for the boys. She welcomed us and gave us a tour of her house. House was clean, well decorated, and most of all...
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From
$300
Per Night
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1 / 14
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1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Dishwasher
  • Refrigerator
  • Stove
  • Patio
  • Parking
  • Grill
  • Microwave
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Bali Hawaii Home is a destination in itself. We built Bali-Hawaii Home with luxury in mind. This is a newly well built home with the best materials.The spacious home with high ceilings was built with inspiration from the modern indoor/outdoor architecture of Bali. Many of our guests are happy to... View all property information
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5 of 5 stars Reviewed May 20, 2014
I would highly recommend the Bali House. It had everything that we wanted and needed. It is like staying in your own little resort. The walk to the beach is very easy and...
4 of 5 stars Reviewed April 7, 2014
Bali Hawaii was spacious and nicely appointed. The three of us had plenty of space to spread out and have privacy. What I liked best was the location--a 5 minute walk to the beach...
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From
$265
Per Night
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (13) Make Inquiry
Amenities & Details
  • Fax
  • Microwave
  • Washer
  • Hot Tub
  • Stereo System
  • Ceiling Fans
  • Dryer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Charming and Newly remodeled 2 Bedroom, 2 Bath Villa on private Beachside Estate with swimming pool and jacuzii. Just a short 2 minute walk to Kailua Beach through the park. Sleeps 4. View all property information
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3 of 5 stars Reviewed July 14, 2014
First of all, the hosts are friendly and helpful. The location of the villa is very convenient to Kailua Beach. There is also a communal washer and dryer which is very handy to...
5 of 5 stars Reviewed January 21, 2014
Quaint beachy atmosphere. Rooms were clean and well cared for. Charming local decor. Sleeps 4 comfortably. The air conditioner worked perfectly. The kitchen was well stocked with...
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From
$285
Per Night
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1 / 26
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7 Bedrooms, 5 Bathrooms, Sleeps 20
Bookings
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Amenities & Details
  • Stove
  • Dryer
  • Parking
  • Air Conditioning
  • Washer
  • Grill
  • Ceiling Fans
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
A short peaceful 5 minute walk to the stunningly beautiful Kailua Beach will leave you in a state of bliss. Indulge yourself in an array of beach activities including swimming, snorkeling, kayaking, windsurfing and sunbathing as the tropical trade-winds pass by taking your worries with them.... View all property information
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4 of 5 stars Reviewed August 25, 2014
Brenda and her co-Horts were so great to work with and very attentive to our needs and request. We had 10 of us and they helped coordinate all the space and rooms we needed to...
5 of 5 stars Reviewed June 11, 2014
We stayed in Palawiki properties with 3-bedroom 2 bath room. The house is spacious , beautiful, lovely and very clean. It is more like a sweet home to my family. The kitchen...
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From
$5,500
Per Night
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1 / 37
10 Bedrooms, 11 Bathrooms, Sleeps 18
Details Reviews (4) Make Inquiry
Amenities & Details
  • DVD Player
  • Pool
  • Safe
  • VCR
  • Internet Access
  • Fitness Room
  • Ceiling Fans
  • Children's Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Oahu Lani is a child-friendly, family-oriented beachfront villa that occupies a superb location on Kailua beach, rated one of the 10 finest beaches in the U.S. This warm and welcoming Oahu vacation rental has 10 bedrooms and can accommodate up to 18 guests, making it an ideal choice for a large... View all property information
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From
$395
Per Night
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1 / 16
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3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (23) Make Inquiry
Amenities & Details
  • Microwave
  • Stove
  • DVD Player
  • Parking
  • Washer
  • Dishwasher
  • Pool
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Beautiful, licensed, newly remodeled 3 Bedrm, 3 Bath Kailua Beach side villa, surrounded with lush tropical gardens, on private estate with swimming pool and jacuzzi.. Just walk down a private beach lane and in less than 2 minutes you would be at the most beautiful beach in the country! It is a... View all property information
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5 of 5 stars Reviewed April 19, 2014
We wanted to celebrate a 50 year anniversary with the whole family and this proved to be the perfect setting! Each family of 4 had their own 'home': one was in Kukui House...
4 of 5 stars Reviewed November 21, 2013
After 5 weeks travelling in the continental US and Canada with 4 children, we thoroughly enjoyed our week at Kukui House Kailua where we could kick back and relax, enjoy day...
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From
$115
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Toaster
  • Washer
  • Refrigerator
  • Parking
  • Towels Provided
  • Internet Access
  • Garden or Yard
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
We have 2 properties located directly across the street from one another with two 1 bedroom/ 1 bathroom units between the two properties as well as a two spacious studios & 4 private rooms. All our units have their own private entrances and outside sitting areas. Both these properties are centrally... View all property information
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5 of 5 stars Reviewed October 29, 2014
I really enjoyed my stay here. The location was close to everything. The room was spacious and clean. The bed was super comfortable. The deal was amazing. I certainly would book...
5 of 5 stars Reviewed August 28, 2014
This studio is very roomy and comfortable with everything needed for a great stay! We did a lot of site seeing on the island, and it was so refreshing to come back to our studio...
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From
$175
Per Night
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1 / 19
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Studio, 1 Bathroom, Sleeps 4
Details Reviews (36) Make Inquiry
Amenities & Details
  • Washer
  • Parking
  • DVD Player
  • Stereo System
  • Dryer
  • VCR
  • Refrigerator
  • Beach Chairs
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Kailua Bay & Mountain Views! Only 100 yards to Kailua Beach Park! This property is located in Kailua, on Windward Oahu. Relax and unwind in this spacious 3rd floor 1000 sq ft studio. Enjoy your morning coffee on the lanai while listening to the breeze, ocean and rambunctious birds. Watch the... View all property information
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5 of 5 stars Reviewed November 1, 2014
best location in o'ahu….. we had a wonderful stay here, we had everything we needed for a perfect vacation. owners were helpful. the place itself is beautiful and spacious…enjoyed...
5 of 5 stars Reviewed June 2, 2014
Just left this morning and hated to leave. The place looks just like the photos. It was very clean and spacious. The outdoor lanai was very nice and spacious as well. The...
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From
$450
Per Night
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1 / 31
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Dryer
  • Microwave
  • Dishwasher
  • Grill
  • Fireplace
  • Garage
  • Parking
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Paradise, across the street is a short path to Kailua Beach, voted #1 beach in America by Conde Nast Traveler Magazine. A beautiful rather secluded beach far less crowed than most beaches in Hawaii. This private home is a home away from home. This 3 bedroom, 3 Bath property is completely... View all property information
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From
$1,350
Per Night
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1 / 19
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • Washer
  • Patio
  • Stereo System
  • DVD Player
  • Dishwasher
  • Fax
  • Sauna
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
***As of August, 2014, the Kailua Beachfront Retreat will require at least 10 night stays year round.*** With over 3,000 square feet of living space, this 6 bedroom, 5 bath, Kailua Luxury Beachfront Retreat is the perfect place for friends and family to gather and enjoy an amazing experience... View all property information
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From
$195
Per Night
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1 / 1
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1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Inquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome. This is it! This is the one you've been looking for. Enjoy sleeping on a comfortable King Size Bed. Convenient location in Kailua, clean and breezy, Air conditioned, Wi-Fi, and Ceiling Fans. Fully-Equipped Kitchen includes, microwave, toaster, coffee maker, 4-burner stove with oven, rice... View all property information
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From
$475
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Parking
  • Patio
  • Washer
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Our Hawaiian-style 3 bedroom 3 bath vacation home is just steps from the sand of beautiful Kailua Beach on the island of Oahu. Hear the sounds of the surf at night and the trade winds through the coconut trees. Relax. Walk on the beach. Swim. Lay in the sun. Enjoy life Hawaiian-style. Our home is... View all property information
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From
$650
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6 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Stove
  • Refrigerator
  • Washer
  • Garage
  • Ceiling Fans
  • Deck
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesnt end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for... View all property information
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From
$350
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Refrigerator
  • Stereo System
  • Dryer
  • Microwave
  • Dishwasher
  • Grill
  • Stove
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Hale Maluhia (House of Serenity) is a kama'aiana style home near Kailua Beach. In a quiet Kailua neighborhood, the home is a quick 5 minute, one block walk to the world famous secluded white sand beach. Relax with friends and family in this child-friendly family home. Experience the warm "old... View all property information
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From
$1,950
Per Night
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1 / 22
4 Bedrooms, 5 Bathrooms, Sleeps 7
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Amenities & Details
  • Ceiling Fans
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kanani O'Ke Kai is a stunningly elegant, yet subtle, oceanfront home only footsteps away from white, sandy Kailua Beach. Step onto your lanai and be rewarded with gorgeous views of the Koolau mountain range and Kailua Bay. From the lawn, watch brillant sunrises melt into morning skies and see the... View all property information
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From
$935
Per Night
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Parking
  • DVD Player
  • Patio
  • Microwave
  • Dryer
  • Dishwasher
  • Stove
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Old Hawaiiana steps from the world-famous, Lanikai Beach, this three bedroom, three bath retreat has the true feel of the Hawaii of yester-year. Hale Maluhia is tropically decorated with all amenities for your comfort. Art work has been hand selected from local artists. Marble and Travertine... View all property information
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From
$330
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • DVD Player
  • Satellite TV
  • Dryer
  • Stove
  • Washer
  • Microwave
  • Refrigerator
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Makana's Place is a three bedroom, two bath home in quaint Kailua Town. This Non-Smoking home is very spacious over 1600 square feet living quarters, which is equivalent to a 4-5 bedroom home. Beautifully decorated with well quality furniture (Koa). Makana's Place features a full kitchen plus... View all property information
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From
$550
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1 / 32
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Garage
  • Parking
  • Dryer
  • Patio
  • Microwave
  • Dishwasher
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Endless Summer Getaway.... the name says it all. This fabulous upgraded three bedroom three bath home boasts pride of ownership along with a feeling of hospitality. As you enter into the home you walk into the living/family room, then straight ahead is the sliding door that leads to the outdoor... View all property information
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From
$450
Per Night
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1 / 10
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Stove
  • Ceiling Fans
  • Parking
  • Internet Access
  • Hot Tub
  • Dryer
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Within half an hour of Honolulu International Airport and Waikiki, this quaint beach house sits on one of the most beautiful beaches in the state of Hawaii - Kailua- miles of white sand, with water sports, dining, sunrise and sunset beach walks, and private hot tub. It is an easy drive to Sea Life... View all property information
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From
$750
Per Night
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1 / 28
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6 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Ceiling Fans
  • DVD Player
  • Outdoor Dining Area
  • Air Conditioning
  • Stereo System
  • Satellite TV
  • Deck
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
With access to the world-famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior maintains a modest aesthetic, but this only serves as a cover of sorts for how... View all property information
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From
$550
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Grill
  • Fireplace
  • Microwave
  • DVD Player
  • Patio
  • Hot Tub
  • Garage
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This Custom beachside home is steps from beautiful Kailua beach. It features a refreshing cobalt blue heated pool and spa, as well as, a gas firepit for those evenings by the pool. As it's a custom home it offers an indoor fire place and vaulted ceilings, wood floors, berber carpet and the... View all property information
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From
$350
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1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Parking
  • Dryer
  • Stove
  • Refrigerator
  • Internet Access
  • Washer
  • Microwave
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and surroundings at your fingertips. This very new rental has been renovated and re-decorated for a clean,... View all property information
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From
$139
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Studio, 1 Bathroom, Sleeps 3
Booking
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Sleep till noon. You'll like the Beach Bungalow at Kailua Guesthouse. This large studio cottage has a California king bed and a queen-size sofa bed. There's a large lanai with park bench and bistro table. Full bath with tub and shower. Complimentary assigned parking on property and laundry... View all property information
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From
$165
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Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Grill
  • Safe
  • Microwave
  • Ceiling Fans
  • Stereo System
  • Dryer
  • Parking
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully... View all property information
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5 of 5 stars Reviewed October 19, 2014
Nancy's Cottage was recommended to us by friends - it was fabulous! My husband, 19yr old daughter and I went to visit our daughter and boyfriend's family. They only lived about...
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From
$900
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5 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Refrigerator
  • Stove
  • Parking
  • DVD Player
  • Patio
  • Dishwasher
  • Stereo System
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to the world of John Walker. A Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). Mr. Walker's inviting presence is felt in the... View all property information
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From
$175
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Studio, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Washer
  • Safe
  • Refrigerator
  • Dryer
  • Stove
  • Patio
  • Microwave
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
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5 of 5 stars Reviewed September 22, 2014
We loved this wonderful spot. It was as described 5 minutes walk to the beach, beautifully presented, immaculately clean. Eveything we needed was there, they have really thought...
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From
$95
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1 / 10
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Studio, 1 Bathroom, Sleeps 2
Booking
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy peace and quiet in this quaint, private cottage with queen-size bed and kitchenette, lovely tropical yard with covered lanai, beach shower, and 1-1/2 blocks to famous Kailua beach. Walking/biking distance to boutiques and restaurants in Kailua town. There is a washer/dryer on premises and... View all property information
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From
$200
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1 / 16
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Studio, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Dryer
  • DVD Player
  • Grill
  • Refrigerator
  • Stereo System
  • Microwave
  • Washer
  • Canoe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
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From
$525
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1 / 27
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4 Bedrooms, 3 Bathrooms, Sleeps 8
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
E Komo Mai! (welcome) Your memorable stay starts as you drive down your private lane into the serenity of a tropical outdoor paradise, providing you with the ultimate island vacation location. Staying true to its Hawaiian charm the 3 bedroom 2 bathroom main home and 1 bed 1 bath separate cottage... View all property information
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From
$475
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1 / 14
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (3) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Grill
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy the charm of Kailua beach in this delightful kama'aina three bedroom home. Just one house back from the sands of Kailua beach on a private loop, this charming Hawaiiana beach house is a tropical oasis. Three wonderfully appointed bedrooms, a modern kitchen, and spacious, beautifully furnished... View all property information
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5 of 5 stars Reviewed August 17, 2014
We stayed here for 7 nights during June of this year. The house was exactly what we were looking for. The location is ideal as it is not more than 1 minute walk from the beach...
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Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.